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Showing metabocard for Allysine (HMDB0001263)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
enzymes (4) Show 4 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 08:57:06 UTC
HMDB IDHMDB0001263
Secondary Accession Numbers
  • HMDB01263
Metabolite Identification
Common NameAllysine
DescriptionAllysine is a derivative of Lysine, used in the production of elastin and collagen. It is produced by the actions of the enzyme lysyl oxidase in the extracellular matrix and is essential in the crosslink formation that stabilizes collagen and elastin.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-amino-5-Formylvaleric acidChEBI
2-Aminoadipate 6-semialdehydeChEBI
6-OxonorleucineChEBI
alpha-Aminoadipic acid delta-semialdehydeChEBI
alpha-Aminoadipic delta-semialdehydeChEBI
hco-[CH2]3-CH(NH2)-COOHChEBI
2-amino-5-FormylvalerateGenerator
2-Aminoadipic acid 6-semialdehydeGenerator
a-Aminoadipate delta-semialdehydeGenerator
a-Aminoadipic acid delta-semialdehydeGenerator
alpha-Aminoadipate delta-semialdehydeGenerator
α-aminoadipate δ-semialdehydeGenerator
α-aminoadipic acid δ-semialdehydeGenerator
a-Aminoadipic delta-semialdehydeGenerator
α-aminoadipic δ-semialdehydeGenerator
a-Aminoadipate δ-semialdehydeGenerator
a-Aminoadipic acid δ-semialdehydeGenerator
a-Aminoadipic δ-semialdehydeGenerator
(2S)-2-amino-6-OxohexanoateHMDB
(2S)-2-amino-6-Oxohexanoic acidHMDB
2-amino-HexanedioateHMDB
2-amino-Hexanedioic acidHMDB
2-amino-Hexanedioic acid semialdhydeHMDB
2-Aminoadipate semialdehydeHMDB
2-Aminoadipate-6-semialdehydeHMDB
5-Formyl-norvalineHMDB
6-oxo-L-NorleucineHMDB
6-oxo-NorleucineHMDB
alpha-Aminoadipic semialdehydeHMDB
L-2-Aminoadipate 6-semialdehydeHMDB
L-6-OxonorleucineHMDB
L-AllysineHMDB
2-Aminoadipic semialdehydeMeSH
alpha-AASAMeSH
alpha-Aminoadipate semialdehydeMeSH
Chemical FormulaC6H11NO3
Average Molecular Weight145.1564
Monoisotopic Molecular Weight145.073893223
IUPAC Name2-amino-6-oxohexanoic acid
Traditional Nameallysine
CAS Registry Number1962-83-0
SMILES
NC(CCCC=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)
InChI KeyGFXYTQPNNXGICT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Alpha-hydrogen aldehyde
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility49.4 g/LALOGPS
logP-2.2ALOGPS
logP-2.9ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)2.25ChemAxon
pKa (Strongest Basic)9.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.96 m³·mol⁻¹ChemAxon
Polarizability14.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-e7c5c166681ba0316b25View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8910000000-8fb215d3dd09e5553352View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufs-2900000000-cc3c3ade4cefc6b57880View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9700000000-1f5f0f3378ed80283ec8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-dd87ab890dceec9e01cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-5623b839bf292d641b92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-4900000000-7473bdea5b2f626515f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-12c42805d877e4f712b6View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.2 uMInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified<1 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1.6-28 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedPyridoxine dependency with seizures (PDE) details
Associated Disorders and Diseases
Disease References
Pyridoxine-dependent epilepsy
  1. Plecko B, Paul K, Paschke E, Stoeckler-Ipsiroglu S, Struys E, Jakobs C, Hartmann H, Luecke T, di Capua M, Korenke C, Hikel C, Reutershahn E, Freilinger M, Baumeister F, Bosch F, Erwa W: Biochemical and molecular characterization of 18 patients with pyridoxine-dependent epilepsy and mutations of the antiquitin (ALDH7A1) gene. Hum Mutat. 2007 Jan;28(1):19-26. [PubMed:17068770 ]
Associated OMIM IDs
  • 266100 (Pyridoxine-dependent epilepsy)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022519
KNApSAcK IDNot Available
Chemspider ID202
KEGG Compound IDC01475
BioCyc IDALLYSINE
BiGG ID1445244
Wikipedia LinkAllysine
METLIN ID6118
PubChem Compound207
PDB IDNot Available
ChEBI ID17027
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Carbonyl reductase [NADPH] 1
General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
Allysine → 2-amino-6-hydroxyhexanoic aciddetails
Enzyme Details
2. Aldehyde oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
Allysine → Aminoadipic aciddetails
Enzyme Details
3. Alpha-aminoadipic semialdehyde synthase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme that catalyzes the first two steps in lysine degradation. The N-terminal and the C-terminal contain lysine-ketoglutarate reductase and saccharopine dehydrogenase activity, respectively.
Gene Name:
AASS
Uniprot ID:
Q9UDR5
Molecular weight:
102130.895
Enzyme Details
4. Acyl-CoA synthetase family member 4
General function:
Involved in acyl carrier activity
Specific function:
Acyl-CoA synthases catalyze the initial reaction in fatty acid metabolism, by forming a thioester with CoA
Gene Name:
AASDH
Uniprot ID:
Q4L235
Molecular weight:
122596.1